R9532

Pyocyanin, Ready Made Solution from Pseudomonas aeruginosa

5 mg/mL in DMSO

• Synonym(s): 5-Methyl-1(5H)-phenazinone, Pyocyanine, Sanasin, Sanazin
• Empirical Formula (Hill Notation): C₁₃H₁₀N₂O
• CAS Number: 85-66-5
• Molecular Weight: 210.23
• MDL number: MFCD01794662
• UNSPSC Code: 12352200
• PubChem Substance ID: 329824047
• NACRES: NA.77

Properties

• assay: ≥98% (HPLC)
• Quality Level: 200
• form: DMSO solution
• concentration: 5 mg/mL in DMSO
• shipped in: dry ice
• storage temp.: −20°C
• SMILES string: CN1c2ccccc2N=C3C(=O)C=CC=C13
• InChI: 1S/C13H10N2O/c1-15-10-6-3-2-5-9(10)14-13-11(15)7-4-8-12(13)16/h2-8H,1H3
• InChI key: YNCMLFHHXWETLD-UHFFFAOYSA-N

Description

General description

Pyocyanin is a secondary metabolite, which is produced by Pseudomonas aeruginosa.

Application

Pyocyanin has been used:

• To disable the ability of forkhead box A2 (FOXA2) to regulate goblet cell hyperplasia and metaplasia (GCHM) and mucin expression.
• To activate nuclear factor (erythroid-derived 2)-like 2 (NRF2) through the reactive oxygen species (ROS)-inducible epidermal growth factor receptor (EGFR)-phosphoinositide 3-kinase (PI3K) cellular signal transduction pathway and its downstream effectors.
• To stimulate Pseudomonas aeruginosa PAO1 cell line adhesion and invasion in human lung carcinoma A549 cells via reactive oxygen species (ROS) production.

Biochem/physiol Actions

Pyocyanin, a redox-active phenazine, is an electron receptor, which stimulates redox cycling in bacteria, liver cells, and human epithlial cell lines. It enhances oxidative metabolism, which increases the formation of intracellular reactive oxygen species (ROS) via reduction of NADPH. Pyocyanin also increases the release of the neutrophil chemoattractant IL-8 by airway epithelial cells both in vitro and in vivo. This involves signal transduction pathways that include oxidants, protein tyrosin kinases and MAP-kinases. IL-8 secretion by these cells is in synergy with inflammatory cytokines. Pyocyanin accelerates neutrophil apoptosis in vitro. Mice infected with a pyocyanin-deficient strain of P. aeruginosa showed elevated levels of neutrophils and neutrophil chemokines and cytokines, as well as compromised bacterial clearance from the lungs compared with mice infected with a wild type strain. This suggests that pyocyanin production by P. aeruginosa suppresses the acute inflammatory response by pathogen-driven acceleration of neutrophil apoptosis and by reducing local inflammation, and that this is advantageous for bacterial survival.

Safety Information

• Storage Class: 10 - Combustible liquids
• wgk_germany: WGK 1
• flash_point_f: Not applicable
• flash_point_c: Not applicable